January 15, 2016

Stage 2: Experimenting

With some experience under your belt, you may have decided on one, or a few, target areas in which to focus your philanthropy, or at least delve further.

With some experience under your belt, you may have decided on one, or a few, target areas in which to focus your philanthropy, or at least delve further. Alternatively, you may simply have honed your thinking by learning what you don’t want to do again. Either way, you have sharpened your priorities. It’s likely that you also know something about the kinds of results you can realistically expect to achieve through your philanthropy. You may also have identified the role you are best suited to play to make change happen. For example, a goal to increase economic empowerment for poor populations may have spurred early investments in micro-lending, but through these pilots, you may have realized that basic healthcare is a bigger impediment to the people you’re trying to support.

Now is the time to put a stake in the ground about where to focus your efforts. Being explicit about your funding choices—and then having the discipline to say no to other things—is a prerequisite if you want to move from exploring to making a long-term, measureable difference.

You are in this stage if…

  • You have learned about your areas of interest and explored with some grants or pilots.
  • You are ready to make some choices about the role of your philanthropy, and how that role drives your funding priorities.

Questions to ask

  • What is in and what is out going forward?
  • What difference will, specifically, my personal contribution make (or what results can I imagine holding myself accountable for)?
  • What resources am I willing to invest?
  • How do I imagine I will work with grantees?
  • What interventions seem likely to yield better results, given my resources?

Things to do

  • Continue to solicit input from experts and practitioners in the field.
  • Conduct due diligence on potential grantees so that you will fund organizations that are aligned with the results that you want to help achieve.
  • Transition away from any activities that you’ve placed on your "do not pursue" list.

Your goals for this stage

  • Develop a strategy, or theory of change, for how you and other people in your field (grantees, other funders, among others) will, together, achieve the results you seek.
  • Identify the specific role your philanthropy will play within that strategy, including a few targets against which you’ll hold yourself accountable.


At this stage, you are starting to define your strategy. One critical piece of strategy is, of course, defining what your goal is. One trap is to become overly wedded to too many metrics. This may be challenging for the organizations you are supporting to manage. Instead, work closely with your grantees to identify the few indicators that really matter, and use the data gathered to inform your decisions about how to get better.

Another trap getting so wrapped up in a highly-engineered grant selection process—complete with criteria, checklists, and all the rest—that you miss the big picture. You want to ensure your grants really do add up to your greater vision of success. To avoid this, make sure you consistently ask "how does this fit into my greater objectives?"

A third trap is to be overconfident and fly solo. In the quest to aim high, some philanthropists become overly optimistic about what their resources can realistically accomplish. As a result, they set unrealistic expectations for grantees, and sow the seeds for poor grantor-grantee relationships, where the grantee can feel continually overwhelmed, and the grantor continually unsatisfied. In addition, you risk missing out on great work being done by others in the field—other funders, fantastic organizations, and government programs—that you can learn from and also build off of to drive the change you collectively seek.

Example Journey: John Simon and the GreenLight Fund

John Simon, a venture capitalist, has always been interested in social action and direct service to communities in need. Simon had experimented with different ways of driving social change — first by founding a non-profit while doing a Rhodes Scholarship in the UK, and next by partnering to build the Steppingstone Foundation geared to bring Prep for Prep, a strong youth development organization, to new cities. While Simon attained success with these ventures, he hit some snags along the way that he used to come up with something totally new.

Simon realized that bringing a successful nonprofit program to a new city required a significant amount of support. Simon’s experience helped him identify "the idea of a systematic ‘idea importer." The importer would help shoulder the huge burdens of execution by fundraising, finding leadership, and providing local insights, thereby enabling more and better replication of programs that had been shown to work. "If a city had one of those," he hypothesized, "it could change in a quantum leap, over a period of years. And what if that organization then replicated itself across many cities? That could revolutionize the whole way that nonprofit ideas spread."

With this germ of an idea, Simon conceived of, and co-founded the GreenLight Fund to do just that in Boston. 

>> Read more about how John Simon’s experimentation with different types of philanthropy and entrepreneurship led to GreenLight

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